Flockhart's acting ability was recognized when William Esper (Mason Gross' theatre director and Flockhart's acting teacher) made an exception to policy by allowing Flockhart to perform on the main stage. Though this venue is usually reserved for juniors and seniors, Harold Scott insisted that Flockhart perform there in his production of William Inge's Picnic. Flockhart graduated with a Bachelor of Fine Arts Degree in Theatre in 1988 as one of only a few students who successfully completed the course. She was inducted into the Rutgers Hall of Distinguished Alumni on May 3, 2003.
After receiving her degree, Flockhart moved to New York City in 1989 where she remained until 1997, living with three other women in a two-bedroom apartment and working as a waitress and aerobics instructor whilst she simultaneously sought auditions.
In spring 1989, Flockhart made her first television appearance in a minor role in an episode of Guiding Light as a babysitter.
She made her professional debut on the New York stage, appearing in Beside Herself alongside Melissa Joan Hart at the Circle Repertory Theatre. Two years later, Flockhart appeared in a television movie, Darrow. Though she later appeared in films Naked in New York (1993) and Getting In (1994), her first substantial speaking part in a film was in Quiz Show, directed by Robert Redford.
Flockhart debuted on Broadway in 1994, as Laura in The Glass Menagerie. Actor Julie Harris felt Flockhart should be hired without further auditions, claiming that she seemed ideal for the part. Flockhart received a Clarence Derwent Award for her performance. In 1995, Flockhart became acquainted with actors such as Dianne Wiest and Faye Dunaway when she appeared in the movie Drunks. Later that year, Flockhart starred in Jane Doe as a drug addict. In 1996, Flockhart appeared as the daughter of Dianne Wiest and Gene Hackman's characters, in The Birdcage. Throughout that year, she continued to work on Broadway, playing the role of Natasha in Anton Chekhov's Three Sisters.
In 1997 Flockhart was requested to audition for the starring role in David E. Kelley's FOX television series, Ally McBeal. Kelley, having heard of Flockhart, wanted her to audition for the contract part. Though Flockhart at first hesitated due to the necessary commitment to the show in a negotiable contract, she was swayed by the script and travelled to Los Angeles to audition for the part, which she won. She earned a Golden Globe Award for the role in 1998.
Flockhart maintained throughout Ally McBeal's run that she has never been diagnosed with either anorexia or bulimia, nor has she been a user of illegal drugs. She did remark, however, that while starring in the show she refrained from eating sweets, retaining her slim figure by working out. She has now admitted that she had a problem at the time, and was 'exercising too much' and 'eating too little'.
Flockhart played the role of Helena in the 1999 film version of Shakespeare's A Midsummer Night's Dream. In 2000, she appeared in Things You Can Tell Just by Looking at Her and Bash: Latter-Day Plays, later accompanying Eve Ensler to Kenya in order to protest violence against women, particularly Female Genital Mutilation. Flockhart also starred in the off-Broadway production of Ensler's The Vagina Monologues.
In 2004, Flockhart appeared as Matthew Broderick's psychotic girlfriend in The Last Shot. In the same year, Flockhart travelled to Spain for the filming of Fragile, which premiered in September 2005 at the Venice Film Festival.
She auditioned for the role of Susan Mayer on Desperate Housewives, but lost the role to Teri Hatcher. A couple of years later, she signed a deal for ABC Television Studio (formerly Touchstone Television) to star in a weekly series (Brothers and Sisters), which is actually the lead-out program too Desperate Housewives.
Flockhart can currently be seen as communication advisor Kitty Walker in the ABC TV prime time series Brothers & Sisters, which premiered in September 2006.
Flockhart has been romantically involved with actor Harrison Ford since meeting him at the 2002 Golden Globe Awards after she spilled wine on his award. The pair were dating within a week. When approached to star in the film Indiana Jones 4, Ford requested that Flockhart co-star as his love interest. Though the film producers agreed, Flockhart is not currently attached to the project. Flockhart's reaction was "Oh, yes. If I could kick his ass, absolutely!" On January 11, 2001, Flockhart adopted a baby boy, born ten days prior, whom she named Liam. Flockhart continues to support charities such as Public Schools Arts, and causes such as breast cancer research. She is the national spokeswoman for Peace Over Violence (POV), which led her to acquire a Humanitarian Award on October 21, 2005.
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